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EP4484437A1 - Procédé de préparation de diphosphites - Google Patents

Procédé de préparation de diphosphites Download PDF

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Publication number
EP4484437A1
EP4484437A1 EP23181668.7A EP23181668A EP4484437A1 EP 4484437 A1 EP4484437 A1 EP 4484437A1 EP 23181668 A EP23181668 A EP 23181668A EP 4484437 A1 EP4484437 A1 EP 4484437A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
aryl
membered ring
variant
atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23181668.7A
Other languages
German (de)
English (en)
Inventor
Anna Chiara SALE
Robert Franke
Dirk Fridag
Peter Kucmierczyk
Ana Markovic
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Oxeno GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evonik Oxeno GmbH and Co KG filed Critical Evonik Oxeno GmbH and Co KG
Priority to EP23181668.7A priority Critical patent/EP4484437A1/fr
Priority to JP2024096524A priority patent/JP7781960B2/ja
Priority to KR1020240081645A priority patent/KR20250000883A/ko
Priority to CN202410826929.3A priority patent/CN119192244A/zh
Priority to US18/754,793 priority patent/US20250011354A1/en
Publication of EP4484437A1 publication Critical patent/EP4484437A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657154—Cyclic esteramides of oxyacids of phosphorus

Definitions

  • the invention relates to a process for the preparation of diphosphites and the compounds used for their preparation.
  • Diphosphites are classically produced using Cl-containing compounds or via CI-containing intermediates.
  • the technical object of the invention is to provide a method in which the problems occurring in connection with the prior art are reduced or eliminated.
  • the object is achieved by a method according to claim 1.
  • Examples of five-membered rings in which one C atom is replaced by one N atom are: pyrrolidine, 2-pyrroline, 3-pyrroline, azole.
  • Examples of five-membered rings in which two C atoms have been replaced by N atoms are: diazolidine, 1,2-diazole, 1,3-diazole.
  • Examples of five-membered rings in which three C atoms have been replaced by N atoms are: 1,2,3-triazolidine, 1,2,4-triazolidine, 1,2,3-triazole, 1,2,4-triazole.
  • Examples of five-membered rings in which four C atoms have been replaced by N atoms are: tetrazolidine, 5H-terazole, 2,5-dihydro-1H-tetrazole.
  • Example of a five-membered ring in which five C atoms have been replaced by N atoms is: 1H-pentazole.
  • the five-membered ring (Y 1 ) has at least one double bond.
  • the five-membered ring (Y 1 ) has two double bonds.
  • the five-membered ring (Y 1 ) has at least one NH bond.
  • the five-membered ring (Y 1 ) has at least two N atoms.
  • the five-membered ring (Y 1 ) has at least three N atoms.
  • the five-membered ring (Y 1 ) has four N atoms.
  • Y 1 stands for the following compound:
  • X 1 is -(C 1 -C 2 )-alkyl.
  • X 1 stands for -CH 2 -CH 3 .
  • X 1 stands for -CH 3 .
  • R 1 , R 2 , R 3 , R 4 are selected from: -H, -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl, -(C 6 -C 10 )-aryl.
  • R 1 , R 2 , R 3 , R 4 are selected from: -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl.
  • R 1 , R 2 , R 3 , R 4 are selected from: -CH 3 , -O-CH 3 , -tert Bu.
  • R 5 , R 6 , R 7 , R 8 are selected from: -H, -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl, -(C 6 -C 10 )-aryl.
  • R 5 , R 6 , R 7 , R 8 are selected from: -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl.
  • R 5 , R 6 , R 7 , R 8 are selected from: -CH 3 , -O-CH 3 , -tert Bu.
  • this includes the additional process step d): d) Addition of a solvent.
  • the solvent is selected from: acetonitrile (ACN), toluene, xylene, THF, heptane.
  • the solvent is acetonitrile (ACN).
  • R 10 , R 20 , R 30 , R 40 are selected from: -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl, -(C 6 -C 10 )-aryl, -CN, -NO 2 and X 2 is -(C 1 -C 6 )-alkyl.
  • R 10 , R 20 , R 30 , R 40 are selected from: -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl.
  • R 10 , R 20 , R 30 , R 40 are selected from: -CH 3 , -O-CH 3 , -tert Bu.
  • X 2 is -(C 1 -C 2 )-alkyl.
  • X 2 is -CH 2 -CH 3 .
  • X 2 is -CH 3 .
  • R 11 , R 22 , R 33 , R 44 are selected from: -H, -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl, -(C 6 -C 10 )-aryl, - CN, -NO 2 and Y 2 represents a five-membered ring in which at least one C atom is replaced by an N atom.
  • R 11 , R 22 , R 33 , R 44 are selected from: -H, -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl, -(C 6 -C 10 )-aryl.
  • R 11 , R 22 , R 33 , R 44 are selected from: -(C 1 -C 12 )-alkyl, -O-(C 1 -C 12 )-alkyl.
  • R 11 , R 22 , R 33 , R 44 are selected from: -CH 3 , -O-CH 3 , -tert Bu.
  • the five-membered ring (Y 2 ) has at least one double bond.
  • the five-membered ring (Y 2 ) has two double bonds.
  • the five-membered ring (Y 2 ) has at least one NH bond.
  • the five-membered ring (Y 2 ) has at least two N atoms.
  • the five-membered ring (Y 2 ) has at least three N atoms.
  • the five-membered ring (Y 2 ) has four N atoms.
  • Y 2 stands for the following residue:
  • the new synthesis route makes it possible to dispense with compounds containing Cl. This saves the time-consuming purification of the diphosphite after synthesis and also avoids the introduction of residual Cl into the reactor.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
EP23181668.7A 2023-06-27 2023-06-27 Procédé de préparation de diphosphites Pending EP4484437A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP23181668.7A EP4484437A1 (fr) 2023-06-27 2023-06-27 Procédé de préparation de diphosphites
JP2024096524A JP7781960B2 (ja) 2023-06-27 2024-06-14 ジホスファイトの調製方法
KR1020240081645A KR20250000883A (ko) 2023-06-27 2024-06-24 디포스파이트의 제조 방법
CN202410826929.3A CN119192244A (zh) 2023-06-27 2024-06-25 制备二亚磷酸酯的方法
US18/754,793 US20250011354A1 (en) 2023-06-27 2024-06-26 Process for preparing diphosphites

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP23181668.7A EP4484437A1 (fr) 2023-06-27 2023-06-27 Procédé de préparation de diphosphites

Publications (1)

Publication Number Publication Date
EP4484437A1 true EP4484437A1 (fr) 2025-01-01

Family

ID=87003031

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23181668.7A Pending EP4484437A1 (fr) 2023-06-27 2023-06-27 Procédé de préparation de diphosphites

Country Status (5)

Country Link
US (1) US20250011354A1 (fr)
EP (1) EP4484437A1 (fr)
JP (1) JP7781960B2 (fr)
KR (1) KR20250000883A (fr)
CN (1) CN119192244A (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004076464A2 (fr) * 2003-02-27 2004-09-10 Mitsubishi Chemical Corporation Phosphites et phosphoramidites optiquement actifs et dotes d'un squelette biphenol a chiralite axiale, leur utilisation dans des reactions catalytiques asymetriques
WO2012095255A1 (fr) 2011-01-13 2012-07-19 Evonik Oxeno Gmbh Procédé de purification de biphephos
WO2014056732A1 (fr) * 2012-10-12 2014-04-17 Evonik Industries Ag Procédé de production d'aldéhydes c5 stable à long terme
WO2015011132A2 (fr) * 2013-07-23 2015-01-29 Evonik Industries Ag Dérivés de phosphoramidite dans l'hydroformylation de composés insaturés
CN116063351A (zh) * 2021-11-01 2023-05-05 中国石油化工股份有限公司 一种亚磷酰胺酯的制备方法及其应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005500B1 (fr) * 1978-05-18 1981-10-07 Ciba-Geigy Ag Dioxaphosphépines, leur préparation et leur utilisation comme stabilisateurs de matières organiques
EP3029053A1 (fr) 2014-12-04 2016-06-08 Evonik Degussa GmbH Monophosphites présentant du naphtol
CN112442087A (zh) 2020-11-26 2021-03-05 上海簇睿低碳能源技术有限公司 一种离子型亚膦酰胺类配体的制备方法及其应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004076464A2 (fr) * 2003-02-27 2004-09-10 Mitsubishi Chemical Corporation Phosphites et phosphoramidites optiquement actifs et dotes d'un squelette biphenol a chiralite axiale, leur utilisation dans des reactions catalytiques asymetriques
WO2012095255A1 (fr) 2011-01-13 2012-07-19 Evonik Oxeno Gmbh Procédé de purification de biphephos
WO2014056732A1 (fr) * 2012-10-12 2014-04-17 Evonik Industries Ag Procédé de production d'aldéhydes c5 stable à long terme
WO2015011132A2 (fr) * 2013-07-23 2015-01-29 Evonik Industries Ag Dérivés de phosphoramidite dans l'hydroformylation de composés insaturés
CN116063351A (zh) * 2021-11-01 2023-05-05 中国石油化工股份有限公司 一种亚磷酰胺酯的制备方法及其应用

Also Published As

Publication number Publication date
CN119192244A (zh) 2024-12-27
KR20250000883A (ko) 2025-01-03
JP2025005405A (ja) 2025-01-16
US20250011354A1 (en) 2025-01-09
JP7781960B2 (ja) 2025-12-08

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